British Travel Award Winners 2020!

We are delighted to announce that we have been awarded 'Best UK Holiday Cottage/Self Catering Booking Company' at the British Travel Awards for an amazing 8th consecutive year.

Dorchester Cottage Holidays

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Your search returned 485 cottages.

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  • Flat 2, 38 Preston Road

    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    This spacious ground-floor apartment is nestled in the gorgeous seaside town of Weymouth in Dorset. Bike/kayak storage. En-suite. WiFi. Dorchester 6.3 miles; Isle of Portland 8.6 miles; West Lulworth 12.3 miles. (Ref. 1037083)

    7 nights from £490

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  • Fleet Breeze

    Wyke Regis, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A fabulous three-storey mid-terrace resting in Wyke Regis, part of Weymouth in Dorset. WiFi. Woodburning stove. Close to amenities. Weymouth 2.4 miles; Dorchester 10 miles. (Ref. 1056401)

    7 nights from £559

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  • Swan Cottage

    Warmwell, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A contemporary mid-terrace property on the Beaumont Village at Silverlake estate in Warmwell, Dorset. Use of onsite facilities. Lakeside location. Underfloor heating. Balcony. Dorchester 5.9 miles; Weymouth 9.8 miles; East Lulworth 11 miles. (Ref. 1064990)

    7 nights from £649

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  • Smugglers Cottage

    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A contemporary, three-storey property resting by the harbour in Weymouth, Dorset. Woodburning stove. WiFi. Close to beach and amenities. Weymouth 1 mile; Dorchester 8.6 miles. (Ref. 1058500)

    7 nights from £618

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    Last booked 2 days ago
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  • Darwin's

    Weymouth, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A charming end-terrace cottage, resting in the popular coastal resort of Weymouth, Dorset. Pet-friendly. Enclosed garden. Close to amenities and beach. Dorchester 7.4 miles; West Lulworth 14.3 miles; Bridport 20.7 miles. (Ref. 1048252)

    7 nights from £618

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  • Townbridge Apartment

    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A gorgeous second-floor apartment nestled at the heart of Weymouth, Dorset. Open-plan living space. Private parking. Close to the coast. Chickerell 3 miles; Dorchester 8.3 miles; Swanage 28.9 miles. (Ref. 1062367)

    7 nights from £564

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  • Nautical Breeze

    Weymouth, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A contemporary second-floor apartment set within the town of Weymouth, Dorset. Close to the close. Balcony with views. Dorchester 8.4 miles; Bridport 19.2 miles; Bournemouth 37.1 miles. (Ref. 1052595)

    7 nights from £526

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  • Emmies

    Osmington near Preston, Dorset
    • Sleeps6
    • Bedrooms3
    • PetsYes
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A charming period cottage positioned in Osmington near Preston. Open fire. Enclosed courtyard. WiFi. Dog-friendly. Weymouth 5.3 miles; West Lulworth 10 miles. (Ref. 1060123)

    7 nights from £696

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    Last booked yesterday
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  • Little Maltings

    Milton Abbas, Dorset
    • Sleeps2
    • Bedrooms1
    • PetsYes
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A quaint holiday cottage resting at the heart of Milton Abbas. Pet-friendly. Off-road parking. Pub nearby. WiFi. Milborne St Andrew 3.1 miles; Blandford Forum 9.1 miles. (Ref. 1064087)

    7 nights from £437

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  • Bindon Cottage

    Wyke Regis, Dorset
    • Sleeps4
    • Bedrooms2
    • PetsNo
    • Sykes rating Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes Icon/Rating/Sykes

    A quaint cottage resting in the village of Wyke Regis in Dorset. Open-plan living. WiFi. Close to shops and pubs. Weymouth 2 miles; Fortuneswell 3.6 miles. (Ref. 1052707)

    7 nights from £483

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Just show me Dorchester Cottages

If you're looking for somewhere with facilities on hand yet close to amazing countryside, our Dorchester cottages make great contenders. Think elegant architecture, historic sites, thriving culture and excellent shopping.

Dorchester's a fantastic place for browsing. Shoppers will find all kinds of specialist shops, high street names and markets, while museums range from dinosaurs, teddies and Chinese Terracotta Warriors, to Roman artefacts and Tutankhamun. And in between shopping and sightseeing, relish delicious snacks and meals in a wide variety of establishments, from pavement cafes to Michelin-starred restaurants.

When it comes to historic sites, Dorchester features a treasure trove of delights. Don't miss the splendid Roman Town House, the home of infamous 'Hanging' Judge Jeffreys, the huge Iron Age hill fort of Maiden Castle and the Roman amphitheatre at Maumbury Rings.

Thomas Hardy's Wessex a stone's throw from your Dorchester cottage

Dorset's wonderful landscapes have inspired many writers and most of Hardy's novels are based on Dorset; Dorchester is indeed the legendary town of 'Casterbridge'. The Dorset County Museum displays his works, while you can also visit his birthplace Hardy's Cottage and his Victorian villa Max Gate, designed by Hardy and built by his brother. Discover more of his beloved 'Wessex' on foot and stride out from your Dorchester cottage along the Dorchester to Weymouth Trail (10 miles).

To the west of the town centre you'll find Poundbury, Prince Charles' award-winning residential development built in the traditional architectural style of Dorchester and home to a variety of attractions, including a monthly farmers' market.